Potassium Carbonate → HCID 178509697, compound

HRID 706011Notes

Reaction equation

OS(C(F)(F)F)(=O)=O.[C:9](=[NH:32])([O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[CH:16][CH:15]=1)[NH2:10].[C:33]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH:42]([CH:48]=O)[C:43](OCC)=[O:44])=[CH:37][CH:36]=1)#[N:34].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][O:11][C:9]3[NH:10][CH:48]=[C:42]([CH2:41][C:38]4[CH:37]=[CH:36][C:35]([C:33]#[N:34])=[CH:40][CH:39]=4)[C:43](=[O:44])[N:32]=3)=[CH:19][CH:18]=2)=[CH:22][C:23]=1[C:28]([F:31])([F:30])[F:29]

Participants

Conditions

Temperature: 160 °C

Procedure

The mixture of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflate (120 mg, 0.236 mmol), ethyl 3-(4-cyanophenyl)-2-formylpropanoate (137 mg, 0.591 mmol) and K2CO3 (98 mg, 0.709 mmol) in DMA (5 mL) was heated with a microwave reactor at 160° C. for 1 hour. Purification via MDAP then afforded the title compound as a pale yellow solid (38 mg, 29.0% yield). LCMS: rt=3.90 min, [M+H+]=526.2

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-f38356a5da92452bb071e860e5ab7ef7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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